🏘️ 14 best short term rental opportunities | December 1, 2023


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This 3 bedroom lakefront in the Northeast is $529k and featured in the Pro version of this newsletter.

On a dead-end private road, tucked away on 5+ acres in the Austerlitz hills, you'll find this truly special architectural retreat. Designed by the noted postmodern architect Penny Wells Yates in 1982, the 2 bedroom/2 bath house is a superb example of that era's rustic-modern chalet aesthetic.  The house was ingeniously designed to maximize every space while creating a magnificent sense of openness and light. Sun pours into the triple-height great room anchored by an impressive woodburning stove whose chimney soars to the ceiling. Sliding doors on the south and west walls open onto a wraparound deck. A striking stairwell connects the spaces on multiple levels of the house. One short flight up sits a perfect WFH nook beneath a huge rhombus window. From there it's a half flight up to the updated kitchen and dining room with its own balcony. At the top of the house is a treehouse loft bedroom and a bathroom that has its own sauna (!). On the lowest level is an ultraprivate bedroom with parklike views and a second bathroom.The house had many updates, including new appliances and countertops, a newly rebuilt deck, and design-forward light fixtures throughout. The location is unbeatable--off a quiet road in one of the most desirable areas of Columbia County, under 10 minutes to Hawthorne Valley Farm, 25 minutes to Great Barrington, and 30 minutes to Hudson.

  • $585,000

  • 2 Bedrooms, 2 Bathrooms

  • Average Daily Rate: $454

  • Expected occupancy rate: 56%

  • Monthly expected income: $7,580

  • Monthly expected expenses: $5,559

  • Monthly expected cash flow: $2,021

  • Expected cash on cash return: 15.2%

Enjoy the quiet of a wooded 1.24 acres off convenient Howard Gap Road, with mountain views everywhere, in a unique, quality-built mid-century modern home featuring a solarium with a hot tub. The interior doors are ash, and the door trims, railings and balusters are all solid mahogany. Current owners have installed hardwood flooring, upgraded lighting to LED throughout along with ceiling fans, added gas logs upstairs and down, and installed new rear steps, hot water heater and invisible fencing.

  • $525,000

  • 3 Bedrooms, 2 Bathrooms

  • Average Daily Rate: $352

  • Expected occupancy rate: 61%

  • Monthly expected income: $6,531

  • Monthly expected expenses: $4,418

  • Monthly expected cash flow: $2,113

  • Expected cash on cash return: 17.6%

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